


for to know if you were my true love or no

by garden of succulents (staranise)



Series: Jack's Excessively Detailed Historical Sexual Fantasies [1]
Category: Check Please! (Webcomic)
Genre: Alternate Universe - Historical, Anal Fingering, Anal Sex, Jack's sexual fantasies frequently include worldbuilding, M/M, Oral Sex, Praise Kink, Rope Bondage, Virgin Fantasy, dubcon, non-con fantasy
Language: English
Status: Completed
Published: 2016-08-03
Updated: 2016-08-03
Packaged: 2018-07-29 01:50:48
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,579
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7665649
Author URL: https://archiveofourown.org/users/staranise/pseuds/garden%20of%20succulents
Summary: <blockquote class="userstuff">
              <p>Alone in his bed on a roadie, Jack cooks up a little fantasy about the 18th century, and being waylaid by a highwayman with a southern drawl.</p>
            </blockquote>





	for to know if you were my true love or no

**Author's Note:**

> On Tumblr [I posted](http://des-zimbits.tumblr.com/post/148380120591), "The kink Jack’s most embarrassed to admit to is his unexplored yearning for historical costume/roleplay. But seriously, the thought of Bitty as an 18th century pirate or highwayman detaining Jack, an innocent merchant’s son from Montréal in knee-breeches and buckled shoes, has kept him warm on MANY a cold roadie night."
> 
> [Luminary-child replied](http://luminary-child.tumblr.com/post/148380158936), "HELLO PLEASE ELABORATE *^*"
> 
>  
> 
> [So I did!](http://des-zimbits.tumblr.com/post/148386340021/luminary-child-des-zimbits-the-kink-jacks)

“I could fling you out of the coach,” the highwayman said, “but on such a cold night as this, that _hardly_  seems gentlemanly.”  He smiled, the moonlight glinting on his pistol.  “If you can pledge your word that you’ll behave, we’ll board as your passengers.  You may even get your coach back by morning.”

“O-of course,” Jack said through nerveless lips.  His driver, an old one-armed man, could not fight, for all that he’d been in the wars against the British with Jack’s father.  And while it was nothing like a true Québec winter this far south, there was enough of a chill to make Jack worry for Henri if they were left on the side of the road until someone found them in the morning.  “But you will bring my driver into the carriage, not leave him exposed to the wind on the box all night.”

The highwayman tilted his head, an odd gesture; Jack had trouble seeing the expression below the shadow of his hat, but he thought it might be an appreciative gesture, or an apologetic one.  “Oh, no,” he drawled regretfully.  “He’ll stay up there.”

“Then let him have the rug I have in here,” Jack begged.  “Please, he’s old, he’s served my family for years.”  Sensing the man’s hesitation, he offered his hands.  “I don’t mean to fight you.  You can bind me if you wish.  I’m not trying to trick you, Henri’s been driving all day, and now you’re diverting us from our destination.  He’s cold.  He’s tired.”

Slowly, the highwayman drew a loop of rope from out of his belt, keeping his pistol squarely aimed at Jack’s chest.  It made him nervous; even if the man had no intention to fire, Jack knew the gun could easily discharge by accident if it was even jostled.

“Put this on one wrist,” the highwayman said.  “Draw it tight.  Loop the end around your other wrist, and draw it through the first.”

Jack complied, binding his wrists; then the highwayman changed hands with his pistol and stepped closer, resting the mouth of his gun against Jack’s chest.  Without looking, he pulled the rope more snug, then passed the end through the loops several times before tying it in a series of decisive knots.  Jack felt the gust of the man’s breath on his hands.

“Move back, then,” the highwayman said.  “Put the rug near the door, and move to the furthest corner of the coach.”

Jack did what he was told and stayed there, testing his hands against the sharp and unforgiving bite of the hemp.  Past the door of the coach, the highwayman tossed the rug up to his confederate on the driver’s box, making the horses stamp and toss their heads uneasily.  “All right, Henri?” Jack called.

“As well as can be, Monsieur,” his servant replied, and Jack grimaced from the truth of it.

The highwayman was, in truth, so slight a man that the coach barely moved as he swung himself up into it.  The pistol remained out as he closed and latched the door, but once he reached up and knocked on the roof to tell his driver to move on, and the coach rocked into motion, he uncocked the gun and set it down.  Jack only saw the barest outline of the man’s sleeve in the moonlight as he did it, so he didn’t know if it was on the seat, in his pocket, or down his boot; and then the man reached over to pull down the shade, first on the far side of the coach, and then brushing past Jack to cover the window next to him, leaving them in almost total darkness.

Skin prickling with danger, Jack heard and felt more than saw the highwayman remove his hat and exhale, having achieved some measure of safety for himself.  Jack tried to piece together a picture in his mind: hair spilling out of its binding and around a cleanshaven face.  Sounds that might be the untying and unwinding of a cravat.  Innocent, innocuous things, except Jack didn’t trust when dangerous men relaxed.

And then a touch, light fingers on his knee, spidering over his stocking and brushing against the hem of his culottes.  Jack’s breath caught in his throat.

Was it worth screaming?  In a fight, could he overpower this man–grope in the dark for the gun–or try to throw himself out of the carriage?  Could he unlatch the door before the man retrieved his pistol?  And what about Henri, and the armed man on the driver’s box?

The ropes bit into his wrists.

With the highwayman’s hand on his knee, Jack said slowly, “You have been very gentlemanly.”

“Mm, yes,” the man drawled.  His hand didn’t move; its palm rested on Jack’s kneecap.  Its fingers, distressingly, _did,_  tickling almost to the tendon at the back of Jack’s knee.  “I do attempt to comport myself by certain standards. Though tonight, I must say, you have put me to shame.  No one else I rob is more concerned for their servants than saving their own lives.”

Jack tried twice to swallow before he could trust himself to speak.  “You said that if I–complied, you wouldn’t kill us.”

“And you believed me, like a man of honour, and didn’t bother to beg.”  The hand patted his knee twice, then removed itself as the highwayman did a movement like–shedding his coat?  When he moved again there was less of a sound of stiff, bulky cloth; lightly and with only the little noises of the creak of boots, the clink of some kind of hardware at his belt, the breath of exertion, he slid himself down the bench until he was directly opposite Jack.  He reached out and cupped Jack’s cheek with one hand, and the arm that brushed Jack’s lips was covered with the fine lawn of a shirt, not the cuff of a jacket. It was gentle when Jack turned his head, trying to avert his face; it just slid down to his jaw, Jack’s breath ghosting against the heel of the higwayman’s hand, diverted down onto his lips.

“Oh, you lovely man,” the highwayman said.

Jack closed his eyes, trying for some kind of defense, as the highwayman moved again, pressing closer, his hand leaving Jack’s face to catch against the wall of the coach as the man climbed onto him, straddling his lap.  He felt helplessly pinned as those thighs settled on either side of his hips, as a hand came back from bracing against the wall to caress Jack’s face again, as the hair that was indeed slipping out of its tie spilled across his forehead and eyelashes as the highwayman leaned over him, his face tilted forward over Jack’s face tilted back. Jack could smell several scents from him: fresh dirt from a field, and some old sweat, traces of a barber’s powder on that disarrayed hair, the ghost of vetiver clinging in the folds of his clothes.

“Oh, you…” the man said, the heel of his hand moving over Jack’s cheekbone, his other hand reaching down and freeing Jack’s queue from the back of his coat, then grazing fingertips up his neck, behind his ear. He took the swaying of the coach like a movement of a horse, never losing his seat or dislodging from Jack’s lap for a moment.  “Stealin’ a ride from you was the _best_  idea.”

So when the kiss came, in the darkness, Jack was ready for his lips to be plundered.  The highwayman’s lips grazed his and he thought, _I can endure this._   There was helplessness of being bound, weighed down, outarmed, the knowledge that with his penknife unlikely to do any good against the man’s knife and gun it was better not to resist, but there was no _horror_  at the thought of the man’s lips against his.  Embarrassment, uncertainty, worry for the future, he all possessed; but if his safety could be obtained by nothing more than relaxing his lips, allowing this man to lick his mouth and suck small kisses along his jaw, he’d had duties more onerous.

In point of fact, he found, as the highwayman loosed buttons of his waistcoat and slipped a hand in under his shirt, it was easier, more pleasant, to submit, the back of his head hitting the wall of his coach and a small ragged sound coming out of his lips as the highwayman’s fingers found his nipple.  The hand roamed his chest, one side and the other, while Jack bent to expose his throat to the marauding mouth, trying to muffle his breathing.  He hoped to God Henri was asleep, too tired to stay awake; that the driver had his mind on his business, that he didn’t fix his attention to listening to his master ravishing their passenger.

He smothered Jack’s mouth with his own when he unbuttoned his culottes, made Jack’s breath hitch as he slipped a hand inside, and Jack’s hands jerked helplessly at their bindings as the hand pursued its own agenda, separate from anything Jack could have–it was not quite right to say _suggested_  or _desired_ ; but it would have been easier to bear the certainty of being stroked and brought to climax than the hair-prickling uncertainty of not knowing where that hand was going, what it wanted to do.

“You sweet thing,” the highwayman sighed, and the hand withdrew; he moved back, searching his pockets, his coat’s pockets, and Jack realized with shame flushing his cheeks that no matter what that hand wanted to do, _he was going to let it._

The thing the highwayman found was a vial of oil, for after he used it he pressed it into Jack’s hands, fixing Jack’s thumb over the stopper.  Jack wrapped his fingers around it, eyes closed as with one hand the highwayman unbuttoned his culottes in front and back, then tugged them down.

It was something like horror, or something like… not even realizing hands could _go_  there, as oil-slick fingers cupped his balls, then stroked backwards; then that hand repositioned, came being his leg, cupping and kneading his buttock and thigh, then stroking into his crack again.  The panting of Jack’s breath was ragged again, distressed and uncertain, and the highwayman kissed his bare thigh to soothe him, caressed his shaft with his other hand.

“Here,” the highwayman said softly, drawing his hand out for a minute, still caressing him in front.  “I need more oil.  Can you pour it out?”

Hands trembling, not sure of the wisdom of his actions, Jack pried the stopper of the vial out and managed to keep hold of it, then tilted the bottle forward.  The other man cupped his fingers as Jack let one trickle out, then another.  “That much again,” he said, and Jack doubled the amount before he nodded and said that was enough.  Jack bit his lip as he restoppered the oil, questioning himself even as he slid his hips forward on the bench, propping one foot up on the bench opposite.  This way the highwayman had better access.

It surprised the other man, he thought, and may have prompted the response; the man pressed his face against Jack’s cock, pressed kisses in a line from its base to its head, distracted for a moment before his other hand remembered to rub the oil against Jack’s opening, twist and search with fingers.

One found its way inside and Jack jerked, threw his head back, eyes wide, mouth open in a silent rictus of surprise; the highwayman froze, holding onto his thigh to stay still against the swaying of the coach, but did not draw his finger out.

With suddenly much more clarity on what this was going to involve, Jack drew in a deep breath, shifted slightly to brace his other leg against the floor, and brought his bound hands up to his face, where he caught an edge of his shirt cuff in his teeth.  The highwayman hesitated for a few seconds more, and Jack almost snapped and told him to get on with it; but just as Jack was realizing that impulse would be audible on the driver’s box if he acted on it, hand and mouth unfroze, finger curling up slightly and lips reaching out to suck Jack’s cock.

Tears leaked from Jack’s eyes as he hung, suspended, between the fingers inside him, questing and stroking and producing small white-hot flashes of pleasure, and the hand on his cock, the mouth that accompanied it, fleeting and elusive and always moving.  Jack held himself open to them, held himself still, gritted his teeth against noise, and cried, silently, his chest straining against sobs.

At length hands and mouth left him, left him burning without release, aching and suddenly empty and alone, and the highwayman leaned up, his clean hand against Jack’s chest, and be breathed, “Are you–?”

Jack brought the back of his hand against the highwayman’s face, and stroked his cheek with a thumb; he leaned his head forward when the highwayman moved forward to kiss him, a full and lustful kiss on Jack’s part, needy and devouring.  The highwayman cradled him, using his arm to cushion Jack’s head, bestowing kisses in his mouth in a way that was comforting, giving.  He used the sleeve of his shirt to wipe the tears from Jack’s face, cheeks and eyes but also his temples and the corners of his mouth; he kissed Jack’s nose, cheekbones, eyebrows.

“Turn over for me,” he said breathlessly after a kiss, and Jack did, without hesitation.  He did it with yearning and– _trust_ , a certainty that the man who’d tied him up would see him through till dawn.  A clarity and a peace that didn’t often happen to him.  A welcome sense of rightness when he passed the bottle back, his forearms braced on the bench and knees on the floor of the coach, and slick fingers slid back into him.

The highwayman did it leaning over him, chest pressed to his back; he nuzzled the back of Jack’s neck, his ears, his hair.  His cock going in was slow and gentle, as much Jack pressing back as him pressing in, and didn’t hurt; it just streaked pleasure into him that he vented in raw, heaving breaths.

Then there was a time when the man thrust into him, a small abrupt bump, and then did it again, jerking Jack’s hips back, and Jack dropped his head and knew what it truly was to be mastered.

 _Don’t,_  he thought, and _Don’t ever stop,_  and _I want,_  and he pressed the knuckles of his hands into his eyelids, and fixed his teeth into the hemp of the rope on his wrists, and reached completion at aching last.

(The dream fades here, thoughts about what to do afterward, about being buttoned back into his pants and left with his coach, temporary passengers on the side of the road vanishing like the frost in the first light of dawn. Jack turns his head slightly, hotel pillow smell filling his nose.  When he can move his arm again he gropes for his phone, unlocks it, squints against its brightness in the dark room.  There, where he left it, is tonight’s picture of Bitty in pyjamas, a laptop and a bowl of popcorn.   _Paper writing party!_  it says.

Jack, not feeling eloquent but wanting Bitty to know he’s thinking of him, sends him a series of blown kisses.)


End file.
